Oxy Containing Reactant Patents (Class 568/361)
  • Patent number: 6201155
    Abstract: A process for the manufacture of a symmetrical, terminally ring-substituted polyenes by reacting a polyene di(O,O-dialkyl acetal) with a cyclic dienol ether in the presence of a Lewis or Brönsted acid, hydrolyzing the condensation product resulting therefrom and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel cyclic dienol ethers, as well as, novel intermediates resulting from the condensation and additional intermediates in this process form further aspects of the invention. The final products are primarily carotenoids, which find corresponding use, e.g., as colorings and pigments for foodstuffs, animal products, etc.
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: March 13, 2001
    Assignee: Roche Vitamins Inc.
    Inventors: Bruno Burdet, August Rüttimann
  • Patent number: 6191312
    Abstract: A process for preparing a bicyclooctanone, in particular 1,5-dialkylbicyclo[3.2.1]octan-8-one, by reacting a bicyclooctanol, in particular dialkylbicyclo[3.2.1]octan-8-ol, with a. a catalyst applied to an active-carbon support and comprising heteropolyoxometallate anions of vanadium, molybdenum and phosphorus, and also a corresponding alkali-metal, alkaline-earth-metal and/or ammonium counter ion, and b. a gaseous, oxygen-containing oxidizing agent.
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: February 20, 2001
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Alfred Hagemeyer, Rolf Peter Schulz, Harald Werner, Uwe Dingerdissen, Klaus Kühlein, Heinz Alexander
  • Patent number: 6184420
    Abstract: Unsaturated ketones of the formulae Ia and Ib are prepared by a process consisting of the combination of the following reactions: a) The conventional reaction of an allyl alcohol of the formula IIa or a propargyl alcohol of the formula IIb with an isopropenyl ether of the formula III with formation of a ketal of the formula IV as a byproduct, b) preparation of the isopropenyl ether of the formula III by reacting a ketal of the formula IV with propyne or allene, or a mixture thereof in the gas phase at elevated temperatures in the presence of a heterogeneous catalyst containing zinc or cadmium together with silicon or oxygen, and c) feeding the ketal of the formula IV formed in the reaction (a) into stage (b) for the preparation of the isopropenyl ether of the formula III again.
    Type: Grant
    Filed: September 10, 1998
    Date of Patent: February 6, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Joaquim Henrique Teles, Norbert Rieber, Klaus Breuer, Dirk Demuth, Hartmut Hibst, Stefan Kaeshammer, Heinz Etzrodt, Wulf Kaiser
  • Patent number: 6166091
    Abstract: 2,3,4-trihydroxycyclopentanone represented by the following formula [I], its optically active substance or salt thereof.
    Type: Grant
    Filed: September 29, 1999
    Date of Patent: December 26, 2000
    Assignee: Takara Shuzo Co., Ltd.
    Inventors: Kaoru Kojima, Katsushige Ikai, Tatsuji Enoki, Nobuto Koyama, Ikunoshin Kato
  • Patent number: 6166257
    Abstract: The present invention relates to a process for the asymmetric hydrogenation of a ketonic compound and derivative.The invention relates to the use of optically active metal complexes as catalysts for the asymmetric hydrogenation of a ketonic compound and derivative.
    Type: Grant
    Filed: March 24, 1999
    Date of Patent: December 26, 2000
    Assignee: Rhodia Chimie
    Inventors: Francois Mathey, Frederic Robin, Francois Mercier, Michel Spagnol
  • Patent number: 6162758
    Abstract: In the dehydrogenation of secondary alcohols in the presence of a catalyst comprising zinc oxide and calcium carbonate at elevated temperature in the gas phase, secondary cyclic alcohols are used and the dehydrogenation is carried out in the presence of hydrogen and a catalyst whose active components comprise from 30 to 60% by weight of zinc oxide and from 40 to 70% by weight of calcium carbonate in the calcite modification.
    Type: Grant
    Filed: September 3, 1998
    Date of Patent: December 19, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Franz Josef Brocker, Michael Hesse, Robert Markl
  • Patent number: 6111125
    Abstract: A process for preparing 4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketones of the general formula I, in particular of the (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone of the formula Ia ##STR1## which is required for preparing the red dye capsorubin which is in demand, starts from 2,2,6-trimethylcyclohexanones of the general formula II ##STR2## where R is hydrogen or a protective group, via the novel intermediates of the general formulae V and VI ##STR3## by diastereoselective epoxidation and reaction of the resulting 7-oxabicyclo[4.1.0]heptanes of the general formula VIII ##STR4## with Lewis acids and, where appropriate, removal of the protective group. Also claimed are the novel intermediates of the formula V and their (1S) and (1R) isomers and those of the formula VIII as well as their (1R,3S,6S), (1S,3S,6R) and (1R,3R,6S) isomers.
    Type: Grant
    Filed: March 3, 1995
    Date of Patent: August 29, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael John, Udo Rheude, Joachim Paust, Joachim Meyer
  • Patent number: 6111144
    Abstract: A process for the preparation of a compound having the formula: ##STR1## in which a compound having the formula: ##STR2## is treated with a base and a silylating agent.
    Type: Grant
    Filed: August 20, 1998
    Date of Patent: August 29, 2000
    Assignee: Florida State University
    Inventors: Robert A. Holton, Phong Vu, Tawfik Gharbaoui, Vincent Reboul
  • Patent number: 6031139
    Abstract: The use of polar organic solvent as the solvent in the direct fluorination, to make an .alpha.-fluoroketone, of an enol ester or enol trialkylsilyl ether of a compound containing a tautomerisable ketone group, the solvent being relatively inert to fluorine and one in which the enol ester or enol trialkylsilyl ether is relatively stable to hydrolysis. Preferably the solvent is anhydrous, e.g. anhydrous acetonitrile. Alternatively commercial formic acid containing 3% water may be used with a said enol ester.
    Type: Grant
    Filed: February 5, 1998
    Date of Patent: February 29, 2000
    Assignee: F2 Chemicals Limited
    Inventors: John Hutchinson, Richard Dickinson Chambers
  • Patent number: 6011182
    Abstract: The present invention relates to a process for preparing 2-cyclo-alkenones of the formula I ##STR1## which comprises subjecting a 2-alkoxycycloalkanone and/or a 2-hydroxyalkanone ketal, in which n is an integer from 0 to 20, m is 0, 1, 2 or 3 and R is alkyl, alkylaryl, aryl, arylalkyl, alkenyl or alkynyl, to an elimination reaction in the gas phase on an acidic heterogeneous catalyst.
    Type: Grant
    Filed: February 1, 1999
    Date of Patent: January 4, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Eiermann, Klaus Ebel, Jorg Botzem
  • Patent number: 6002046
    Abstract: Cyclopropyl alkyl ketones are separated from 3-acyltetrahydrofuran-2-ones by adding an alcohol, water or a water/alcohol mixture to a reaction product containing C.sub.1-4 -alkyl cyclopropyl ketone and 4,5-dihydro-2-alkylfuran by-product and an acid catalyst and reacting the by-product with the added alcohol, water of water/alcohol mixture before, during or after distilling said reaction product; and effectively separating C.sub.1 -.sub.4 -alkyl cyclopropyl ketone from reaction by-products.In the preparation of cyclopropyl alkyl ketones from 3-acyltetrahydrofuran-2-ones very reactive 4,5-dihydro-2-alkylfurans are also produced. By reacting such compounds with nucleophilic compounds, such as alcohols or water, before, during or after distillation of the reaction products, it is possible reliably to separate off the 4,5-dihydro-2-alkylfurans as high-boiling addition compounds.
    Type: Grant
    Filed: March 8, 1999
    Date of Patent: December 14, 1999
    Assignee: Huels Aktiengesellschaft
    Inventors: Manfred Kaufhold, Wolfgang Kleemiss, Udo Jegelka, Michael Korell
  • Patent number: 5998674
    Abstract: Method of producing a bromine compound having an aliphatic unsaturated bond which includes reacting a compound having an aliphatic unsaturated bond represented by the following general formula (1) with bromine:R.sup.1 --O--Ar.sup.1 --Y--Ar.sup.2 --O--R.sup.2 (1)to produce a bromine compound represented by the following formula (2):R.sup.3 --O--Ar.sup.1 --Y--Ar.sup.2 --O--R.sup.4 (2)wherein Ar.sup.1, Ar.sup.2 and Y are the same as defined in the above general formula (1) , and R.sup.3 and R.sup.4 are groups obtained by saturating the unsaturated groups of R.sup.1 and R.sup.2 in the above general formula (1) with bromine, respectively.The reaction is carried out in the presence of a solvent which is inactive in the reaction, and a substantial amount of the heat of reaction is removed from a reaction system by the vaporization of the solvent or bromine. A high-purity bromine compound in high yield which is useful as flame retardant, can be obtained.
    Type: Grant
    Filed: August 21, 1998
    Date of Patent: December 7, 1999
    Assignee: Teijin Chemicals, Ltd.
    Inventors: Yutaka Taketani, Haruhisa Hoshimi, Masanori Monri, Seiichi Tanabe, Yasuhiro Shimidzu
  • Patent number: 5994589
    Abstract: A process for preparing 2,5,6-trimethyl-2-cyclohexen-1-one by reacting diethyl ketone with crotonaldehyde or a compound which is converted under the chosen reaction conditions into crotonaldehyde, in the presence of basic agents at elevated temperature, which comprisesa) simultaneously pumping one mole of crotonaldehyde or one mole of a compound which is converted under the reaction conditions into crotonaldehyde, about 5 to 30 moles of diethyl ketone and the aqueous solution or suspension of a strong base, through separate lines or at least partly in the form of a suitable mixture, continuously into a pressure vessel, which is heated where appropriate and which ensures vigorous mixing, in such a way thatb) the reaction temperature is between 150.degree. C. and 350.degree. C., and the average residence time in the pressure vessel is only about 0.1 second to 20 minutes.
    Type: Grant
    Filed: March 10, 1999
    Date of Patent: November 30, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Detlef Ruff, Wolfram Burst, Wulf Kaiser, Manfred Stroezel
  • Patent number: 5892123
    Abstract: A method is disclosed for catalytically decomposing cyclododecyl hydroperoxide into cyclododecanone and cyclododecanol using a chromium catalyst.
    Type: Grant
    Filed: February 3, 1998
    Date of Patent: April 6, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Howard Wayne Anderson, James Bernard Sieja
  • Patent number: 5728890
    Abstract: A cycloalkylhydroperoxide, preferably having a C.sub.5-20 cycloalkyl group, is decomposed by bringing it into contact with a ruthenium complex of the formula:?RuCl.sub.2 L.sub.n !.sub.m (I)wherein L=a neutral ligand, n=1-4 and m.gtoreq.1, for example, ?RuCl.sub.2 (PPh.sub.3).sub.3 !, to produce a cycloalkanol and cycloalkanone.
    Type: Grant
    Filed: January 30, 1996
    Date of Patent: March 17, 1998
    Assignee: Ube Industries, Ltd.
    Inventors: Toshikazu Hamamoto, Mitsuo Yamanaka, Takato Nakamura, Tetsuro Shimano
  • Patent number: 5723632
    Abstract: The present invention provides a method of synthesizing compounds of formula (I): ##STR1## wherein R and R' are independently (C.sub.1 -C.sub.4)alkyl.
    Type: Grant
    Filed: August 8, 1996
    Date of Patent: March 3, 1998
    Assignees: MGI Pharma, Inc., Regents of the University of California
    Inventor: Trevor C. McMorris
  • Patent number: 5712416
    Abstract: Process for preparing benzoquinones by oxidation of phenols in the presence of a diluent and of an oxygen-transferring catalyst which contains a heavy metal ion bound in a complex, wherein oxygen, hydrogen peroxide, a compound which liberates hydrogen peroxide, an organic hydroperoxide, a percarboxylic acid or peroxomonosulfuric acid or salts thereof are used as oxidizing agent, and wherein the oxygen-transferring catalyst is from the class of iron, manganese or chromium tetraaza?14!annulenes.
    Type: Grant
    Filed: November 27, 1995
    Date of Patent: January 27, 1998
    Assignee: BASF Aktiengesellschaft
    Inventor: Thomas Gessner
  • Patent number: 5654489
    Abstract: There is provided a process for producing an alicyclic diketone compound represented by the formula (1) ##STR1## wherein X is a single bond, --CH.sub.2 --, --C(CH.sub.3).sub.2 --, --O-- or --SO.sub.2 --, R.sup.1 and R.sup.2 each represents an alkyl group having 1 to 6 carbon atoms, m and n are 0 to 2, comprising dehydrogenating an alicyclic diol compound represented by the formula (2) ##STR2## wherein X, R.sup.1, R.sup.2, m and n are as defined above in a liquid phase in the presence of at least one member selected from the group consisting of copper type catalysts and Raney type catalysts.
    Type: Grant
    Filed: July 21, 1995
    Date of Patent: August 5, 1997
    Assignee: New Japan Chemical Co., Ltd.
    Inventors: Shuji Kawai, Noboru Araki, Hiroshi Itoh
  • Patent number: 5625099
    Abstract: Abstract of the Disclosure: Compounds of the formula I ##STR1## where R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, R.sup.2 is C.sub.1 -C.sub.4 -alkyl and R.sup.3 is an ether, silyl ether or acetal protective group which can be converted into a hydroxyl group by hydrolysis, in particular one of the radicals ##STR2## and a process for preparing these compounds by reacting an alkenyne of the formula II ##STR3## in an inert solvent in the presence of lithium amide with a cyclohexenone of the formula III ##STR4## and the use of the compounds of the formula I for preparing astaxanthin, are described.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: April 29, 1997
    Inventors: Hansgeorg Ernst, Walter Dobler, Joachim Paust, Udo Rheude
  • Patent number: 5600014
    Abstract: There are described novel biocatalytic and chemical processes for the synthesis of various oxygenated compounds. Particularly, there are described processes for the synthesis of a useful synthon 12 made by reacting a protected diol (acetonide) with permaganate under appropriate conditions. Such synthon is useful of the synthesis of various pharmaceutically important compounds such as D-chiro-inositol and D-chiro-3-inosose. Also, there are disclosed novel compounds, including specifically the synthon 12 and compounds derived therefrom.
    Type: Grant
    Filed: March 24, 1995
    Date of Patent: February 4, 1997
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: Tomas Hudlicky, Martin Mandel
  • Patent number: 5446203
    Abstract: Alternative methods for synthesizing haloenones and haloakenes and their use as starting materials for synthesis of substituted or unsubstituted alkyl and aryl substituted enones and alkenes, including tamoxifen and tamoxifen analogs, using such haloenones and haloalkenes.
    Type: Grant
    Filed: July 29, 1993
    Date of Patent: August 29, 1995
    Assignee: New York University
    Inventor: Edward McNelis
  • Patent number: 5360937
    Abstract: Bisketals of 1,3-cyclobutanedione with monovalent and divalent alcohols as well as processes for their production from 1,3-cyclobutanedione or from 3-acetoxy-2-cyclobuten-1-one contained in the distillation residues of the diketene production. The bisketals are suitable intermediate products for the production of squaric acid, for the production and/or purification of 1,3-cyclobutanedione, or as a stable form for storage or substitute for this unstable dione.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: November 1, 1994
    Assignee: Lonza Ltd.
    Inventor: Barry Jackson
  • Patent number: 5276176
    Abstract: Described are alpha, 3,3-trimethyl-1-cyclohexen-1-methanol derivative-containing composition having from about 85 up to about 90% by weight of a compound having the structure: ##STR1## and from about 10 up to about 15% by weight of a compound having the structure: ##STR2## wherein R.sub.1 is hydrogen or methyl and R.sub.2 is hydrogen or acetyl with the proviso that when R.sub.1 is methyl, R.sub.2 is hydrogen; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations; as well as processes for preparing said alpha, 3,3-trimethyl-1-cyclohexen-1-methanol derivative-containing composition.
    Type: Grant
    Filed: January 8, 1993
    Date of Patent: January 4, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventor: Anthony T. Levorse, Jr.
  • Patent number: 5266729
    Abstract: A process for the preparation of tricyclo[5.2.1.0.sup.2,6 ]decan-8(9)-one by the conversion of 8(9)-hydroxytricyclo[5.2.1.0.sup.2,6 ]dec-3-ene by means of a supported catalyst containing nickel and magnesium oxide at elevated temperature and, if necessary, at elevated pressure.
    Type: Grant
    Filed: August 18, 1992
    Date of Patent: November 30, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hanswilhelm Bach, Werner Kohl, Gregor Deckers, Detlef Kampmann, Claus Kniep
  • Patent number: 5227530
    Abstract: Conversion of alcohol to organic compounds which comprises contacting the alcohol with a heterogeneous catalyst composition comprising crystallineCu.sub.2-X Cr.sub.y Al.sub.6-y B.sub.4 O.sub.17 M.sub.m M'.sub.nwhere M is a divalent metal, M' is a monovalent metal, m is a number in a range from 0 to 0.8, n is a number in a range from 0 to 1.6, X is a number in a range from 0 to 10 0.8 and is equal to the sum of m and n/2, and y is a number in a range from 0.01 to 3, having a characteristic X-ray diffraction pattern.
    Type: Grant
    Filed: March 24, 1992
    Date of Patent: July 13, 1993
    Assignee: Amoco Corporation
    Inventors: Larry C. Satek, Patrick E. McMahon
  • Patent number: 5206442
    Abstract: The preparation of .alpha.,.beta.-unsaturated aldehydes and ketones IO.dbd.C(R.sup.1)--CR.sup.2 .dbd.CR.sup.3 R.sup.4 Iis carried out by acid hydrolysis of cyclic .alpha.,.beta.-unsaturated acetals II ##STR1## in the presence of saturated aldehydes.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: April 27, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Christiane Mackenroth, Ernst Buschmann
  • Patent number: 5200538
    Abstract: The present invention provides an optically active 2-methylenecyclopentanone derivative represented by the general formula ##STR1## (wherein R.sup.1 is a protective group for hydroxyl, and the symbol * represents as asymmetric carbon atom).
    Type: Grant
    Filed: May 27, 1992
    Date of Patent: April 6, 1993
    Assignee: Daiso Co., Ltd.
    Inventors: Takashi Takahashi, Yoshikazu Takehira
  • Patent number: 5164365
    Abstract: The present invention concerns the novel odorant 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone, I, a process for the manufacture of I, novel intermediates used in the process and fragrance compositions containing I. ##STR1## The process for the manufacture of 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone comprises hydroborating 1,1,2,3,3,6-hexamethyl-4,7-dihydroindane and oxidizing the hydroboration product to 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone, or reductively alkylating, especially methylating, 5-nitro-1,1,2,3,3,6-hexamethylindane and converting the resulting 5-dialkyl-amino-1,1,2,3,3,6-hexamethylindane into 1,1,2,3,3,6-hexamethyl-4,5,6,7-tetrahydro-5-indanone by reduction of the benzene ring and hydrolysis of the resulting enamine.
    Type: Grant
    Filed: February 26, 1991
    Date of Patent: November 17, 1992
    Assignee: Givaudan Corporation
    Inventors: Jean-Pierre Bachmann, Daniel Helmlinger, Mario Pesaro
  • Patent number: 5113021
    Abstract: A process for the manufacture of .alpha.- and .beta.-irone, namely the compounds of formula I, as well as novel intermediates in the process is provided.
    Type: Grant
    Filed: September 6, 1990
    Date of Patent: May 12, 1992
    Assignee: Givaudan Corporation
    Inventors: Georg Frater, Daniel Helmlinger
  • Patent number: 5103066
    Abstract: The invention relates to a catalytic dehydrogenation of alcohols to produce ketones and/or aldehydes. The catalyst comprises a dehydrogenation metal and a non-acidic microporous crystalline material as a support. The support may contain indium, tin, thallium or lead, when the dehydrogenation metal is a Group VIII metal.
    Type: Grant
    Filed: December 10, 1990
    Date of Patent: April 7, 1992
    Assignee: Mobil Oil Corp.
    Inventor: Ralph M. Dessau
  • Patent number: 5101077
    Abstract: A process is provided for the preparation of unsaturated carbonyl compounds having at least one cycloalkenic moiety in the molecule, which comprises contacting an allylic type unsaturated alcohol and a conjugated diene in the presence of a catalyst system obtainable by combining a Group VIII metal compound and a ligand containing one or more donor atoms selected from Group V A and VI A elements.
    Type: Grant
    Filed: March 13, 1991
    Date of Patent: March 31, 1992
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 5087760
    Abstract: A process for the production of 1,3-cyclopentanedione, which is a versatile intermediate product for numerous active ingredient syntheses. For this purpose, a malonic acid ester is reacted with a haloalkoxybutenoic acid ester, the resultant bis-(alkoxycarbonyl) alkoxypentenoic acid ester is cyclized to alkoxycarbonyl alkoxycyclopentenone, the ester function is saponified, and finally the intermediate is decarboxylated to the end product.
    Type: Grant
    Filed: January 3, 1990
    Date of Patent: February 11, 1992
    Assignee: Lonza Ltd.
    Inventors: Rudolf Fuchs, John McGarrity
  • Patent number: 5041678
    Abstract: Optically active isomers of alpha-damascone of formula ##STR1## wherein the wavy line designates a C--C bound of cis or trans configuration and its 3-buten-1-one derivative are new compounds having utility in the perfume and flavor industry. They can be prepared starting from an enolate of formula ##STR2## where the wavy line has the meaning given above and Me designates an alkali metal, preferably lithium or magnesium, by treating said enolate with a bifunctional nitrogen derivative of formula ##STR3## where the asterisk identifies a center of chirality;index n stands for zero or 1;each of symbols R.sup.0 and R.sup.1 defines a linear or branched alkyl or aralkyl radical, or one of them represents a hydrogen atom and the other an alkyl radical as defined above;each of symbols R.sup.2 and R.sup.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: August 20, 1991
    Assignee: Firmenich S.A.
    Inventors: Charles Fehr, Jose Galindo
  • Patent number: 4929762
    Abstract: A phenol and/or a cyclohexanone is prepared by dehydrogenation of cyclohexenone and/or a cyclohexenol in liquid phase under the presence of a solid catalyst comprising a platinum-group metal loaded on a carrier. The solid catalyst comprises a carrier selected from activated carbon and hydrotalcites.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: May 29, 1990
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Fujihisa Matsunaga, Hiroshi Fukuhara
  • Patent number: 4918239
    Abstract: This invention provides a method for producing cyclohexanone from cyclohexanol using oxidative dehydrogenation. More particularly, this invention comprises adding a certain amount of a gaseous oxidant to the cyclohexanol feed stream; and, converting the cyclohexanol to cyclohexanone over a CuO-ZnO catalyst.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: April 17, 1990
    Assignee: National Science Council
    Inventors: Ikai Wang, Yu-Ming Lin
  • Patent number: 4898988
    Abstract: A process for the preparation of .beta.-hydroxyketones comprising the catalytic hydrogenolysis of an aqueous solution of isoxazolines having the formula ##STR1## in a fixed bed reactor containing a transition metal catalyst at a temperature between 20.degree. to 150.degree. C. and a pressure from about 0 to 150 psig; wherein R.sub.1 and R.sub.2 are independently selected from hydrogen, alkyl, cycloalkyl or aromatic group and wherein the aqueous solution of isoxazolines is substantially free of acids or buffers.
    Type: Grant
    Filed: March 13, 1989
    Date of Patent: February 6, 1990
    Assignee: W. R. Grace & Co.-Conn.
    Inventors: You-Jyh Lin, Harold Kloczewski
  • Patent number: 4868337
    Abstract: A process for synthesizing an optically pure ketone comprising the steps of: treating an appropriate optically pure boronic ester with an organolithium compound at -78.degree. C. to obtain the "ate" complex, separating the optically pure borinic ester from the complex and converting said borinic ester into an optically pure ketone represented by the formulae:R*COR.sup.1 and R*COC.tbd.CR.sup.1wherein R* is a chiral organyl moiety and R.sup.1 is an achiral organyl moeity.
    Type: Grant
    Filed: December 17, 1987
    Date of Patent: September 19, 1989
    Assignee: Aldrich-Boranes, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 4846945
    Abstract: Oxidation of alcohols to ketones using bromine suffers from a side reaction of comparable speed in which a bromide substituted product is formed. Additionally, the use of bromine as reagent is relatively unpleasant and it creates a major waste disposal problem.The latter problem can be solved by generating bromine in situ by reaction between hydrogen peroxide and bromide ions or hydrogen bromide, but this inevitably increases the exposure of the alcohol to HBr/Br.sup.-. The selectivity of the process towards non-substituted oxidation depending upon the inherent deactivation or reactivity of the alcohol can be improved by irradiating the reactants with light of suitable frequency to generate bromine radicals in the mixture, and/or by controlling the rate of introduction of the hydrogen peroxide and controlling the extent to which mole ratio of HBr:alcohol is substoichiometric.
    Type: Grant
    Filed: September 2, 1987
    Date of Patent: July 11, 1989
    Assignee: Interox Chemicals Limited
    Inventors: Philip J. Turner, Vincent I. Routledge, Martin Jeff
  • Patent number: 4701540
    Abstract: A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: October 20, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
  • Patent number: 4670605
    Abstract: A catalyst and a process to convert commercial cyclohexanol feed to cyclohexanone at a relatively low temperature at stable conversion levels for long periods of operation. This process and catalyst allow operation in the presence of water and high boiling side products. The process features high conversion efficiency and low by-product formation, by use of an improved CuO-ZnO catalyst promoted with an alkali-metal compound such as sodium carbonate. The catalyst is stable in the presence of water and heavy end products in the feedstock (up to 13%). The presence of water rejuvenates the catalyst, increases the conversion and decreases the phenol content in the product mixture.
    Type: Grant
    Filed: May 31, 1985
    Date of Patent: June 2, 1987
    Assignee: Industrial Technology Research Institute
    Inventors: Horn-Ming Chiu, Min-Hon Rei
  • Patent number: 4628120
    Abstract: A preparing method of optically active ketones given by a general formula ##STR1## (wherein R represents a hydrocarbon group having 2 to 20 carbon atoms and R' represents a hydrocarbon group having 1 to 20 carbon atoms. The hydrocarbon groups of R and R' may contain functional groups having no influence on the reaction. But, * represents an asymmetric carbon atom, and R represents a more electron donating group than R' (except when R=R') through the rearrangement reaction by using organoaluminum compound.
    Type: Grant
    Filed: October 16, 1984
    Date of Patent: December 9, 1986
    Assignee: Toyo Stauffer Chemical Co., Ltd.
    Inventors: Genichi Tsuchihashi, Keisuke Suzuki
  • Patent number: 4618724
    Abstract: This invention deals with the use of a perfluorocarbon polymer oxidation catalyst consisting of a perfluorocarbon main chain and a side chain constructed from structural units of chromium (III) difluoromethylene sulfonate or cerium (IV) difluoromethylene sulfonate in a method of preparing a carbonyl compound through an oxidation of an alcohol.
    Type: Grant
    Filed: February 11, 1985
    Date of Patent: October 21, 1986
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Hitosi Nozaki, Koichiro Oshima
  • Patent number: 4616095
    Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloakyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.
    Type: Grant
    Filed: August 13, 1985
    Date of Patent: October 7, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
  • Patent number: 4615830
    Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.
    Type: Grant
    Filed: August 13, 1985
    Date of Patent: October 7, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
  • Patent number: 4613706
    Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.
    Type: Grant
    Filed: August 13, 1985
    Date of Patent: September 23, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
  • Patent number: 4560804
    Abstract: An improved process is provided for forming ketones from the corresponding olefins by vapor phase oxidation of the olefin in the presence of water vapor, and optionally in the additional presence of molecular oxygen employing a heterogeneous catalyst comprising at least one member selected from the group consisting of Ce, Nd and La and compounds and complexes thereof, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4560805
    Abstract: An improved process is provided for forming ketones from the corresponding olefins in the vapor phase in the presence of water vapor employing a heterogeneous catalyst comprising rhenium compounds and complexes, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.
    Type: Grant
    Filed: July 25, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4556742
    Abstract: .alpha.,.delta.-Diethylenic carbonyl compounds of the formula ##STR1## are made by an oxy-Cope rearrangement of an acetylenic alcohol of the formula ##STR2## in the presence of a catalyst based on a metal of Group Ib of the periodic table or palladium. In the formulae (I) and (II), R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be identical or different, each denote a hydrogen atom or a hydrocarbon radical R.sub.2 and R.sub.3 being capable together of forming an alkylene radical (--CH.sub.2 --).sub.n in which one or more carbon atoms may be substituted by one or more alkyl radicals containing 1 to 4 carbon atoms, n is 3 to 20 inclusively and R.sub.5 denotes a hydrogen atom.
    Type: Grant
    Filed: May 25, 1984
    Date of Patent: December 3, 1985
    Assignee: Rhone-Poulenc Sante
    Inventors: Norbert Bluthe, Armand S. Falou, Jacques Gore
  • Patent number: 4550211
    Abstract: Process for the preparation of the compounds of the formulae Ia and Ib ##STR1## wherein A. 2,4,4-trimethylcyclohex-2-en-1-one oxime of the formula IIb ##STR2## is treated with a strong aqueous acid at from 30.degree. to 80.degree. C., preferably 40.degree. to 70.degree. C.,B. the resulting ketone of the formula IIIb ##STR3## is oxidized in a conventional manner, and C. if desired, the resulting compound Ib is isomerized in a conventional manner.Compounds of the formula A ##STR4## where R is one of the following radicals: --CH(OH)--CH.sub.2 --CH.dbd.CH.sub.2 (IIIb), --CH(OH)--CH.sub.3 (IIIc), --CH.sub.2 OH (IIId), --CH(OH)--CH.dbd.CH.sub.2 (IIIe), --CH(OCOCH.sub.3)--CH.sub.3 (IIIf), --CH.sub.2 --OCOCH.sub.3 (IIIg), --CO--CH.sub.2 --CH.dbd.CH.sub.2 (Ib), --CO--CH.sub.3 (Ic) and --CO--CH.dbd.CH.sub.2 (Ie).The compounds IIIb to IIIg, Ib, Ic and Ie are useful scents and aromas, and furthermore may become important intermediates for novel carotenoids.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: October 29, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Janitschke, Werner Hoffmann
  • Patent number: 4532347
    Abstract: The instant invention relates to a membrane solvent extraction and reaction system. More particularly it pertains to an improvement in the membrane solvent extraction system wherein a solute is extracted through a polymeric membrane from one solvent liquid phase to an extracting solvent liquid without direct contact between the liquid phases which are separated by the membrane and in which the extracting solvent has no greater solubility and usually substantially less solubility for the solute than the feed solvent. The impovement comprises converting the solute permeating across the membrane to a different chemical compound, whereby a high concentration gradient for the solute across the membrane is maintained to improve the separation of the solute from the feed solvent liquid phase.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: July 30, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan